Selective hydrogenation of unprotected indole to indoline over N-doped carbon supported palladium catalyst

Deng, Dongshun; Han, Guoqiang; Zhu, Xiao; Xu, Xuan; Gong, Yutong; Wang, Yong

doi:10.1016/j.cclet.2014.12.001

Cited by 10 publications

(3 citation statements)

References 51 publications

(31 reference statements)

Supporting

Mentioning

Contrasting

Order By: Relevance

“…Most likely, the lack of diastereoselectivity (or very poor diastereoselectivity) was due to the fact that the addition of the hydrogen to the iminium-like intermediate formed during the hydrogenation process can occur on either face with no preference. 62 In view of these results, determining the mechanism of isomerization at each step in the reaction was deemed important. The first double bond to be hydrogenated is the exocyclic bond, forming intermediate 10, which is still aromatic (see Table 2 and Scheme 6).…”

Section: ■ Results and Discussionmentioning

confidence: 99%

“…We observed that the hydrogenation reaction with the Z isomer was faster than that with the E isomer; however, in both cases, we failed to observe any diastereoselectivity in the process, and the indolines were obtained in 82% yield from both reactions (Scheme ). Most likely, the lack of diastereoselectivity (or very poor diastereoselectivity) was due to the fact that the addition of the hydrogen to the iminium-like intermediate formed during the hydrogenation process can occur on either face with no preference …”

Section: Resultsmentioning

confidence: 99%

See 1 more Smart Citation

Palladium-Mediated Oxidative Annulation of δ-Indolyl-α,β-Unsaturated Compounds toward the Synthesis of Cyclopenta[b]indoles and Heterogeneous Hydrogenation To Access Fused Indolines

et al. 2019

View full text Add to dashboard Cite

The cyclopenta[b]indole moiety represents a key skeletal unit in several natural and synthetic compounds that exhibit diverse biological properties. We described herein a two-step sequence for synthesizing cyclopenta[b]indoles with great structural diversity in overall yields up to 37%. The key step was a palladium-catalyzed oxidative annulation of 3-alkylindoles (Fujiwara–Moritani reaction). The obtained cyclopenta[b]indoles were used as substrates in heterogeneous hydrogenation reactions to afford new fused indolines in moderate yields. An acid-catalyzed intramolecular cyclization of three such indolines gave tetracyclic lactams in 89, 90, and 61% yields.

show abstract

Section: ■ Results and Discussionmentioning

confidence: 99%

Section: Resultsmentioning

confidence: 99%

Palladium-Mediated Oxidative Annulation of δ-Indolyl-α,β-Unsaturated Compounds toward the Synthesis of Cyclopenta[b]indoles and Heterogeneous Hydrogenation To Access Fused Indolines

et al. 2019

View full text Add to dashboard Cite

show abstract

“…Rh complex catalyzed reduction of indole was reported in the literature (Kuwano et al 2006). Similarly, other catalysts such as Pd/ C (Deng et al 2015) and LiAlH 4 (Leete and Marion 1953) were used for the reduction of indoles. The literature survey indicates that the AC-Ni catalyst system has not used for the reduction of indole.…”

Section: Introductionmentioning

confidence: 96%

Synthesis, characterization and catalytic activity of nanosized Ni complexed aminoclay

Ranchani

Parthasarathy

Devi³

et al. 2017

Appl Nanosci

View full text Add to dashboard Cite

A novel Ni complexed aminoclay (AC) catalyst was prepared by complexation method followed by reduction reaction. Various analytical techniques such as FTIR spectroscopy, UV-visible spectroscopy, DSC, TGA, SEM, HRTEM, EDX, XPS and WCA measurement are used to characterize the synthesized material. The AC-Ni catalyst system exhibited improved thermal stability and fiber-like morphology. The XPS results declared the formation of Ni nanoparticles. Thus, synthesized catalyst was tested towards the Schiff base formation reaction between various bio-medical polymers and aniline under air atmosphere at 85°C for 24 h. The catalytic activity of the catalyst was studied by varying the % weight loading of the AC-Ni system towards the Schiff base formation. The Schiff base formation was quantitatively calculated by the 1 H-NMR spectroscopy. While increasing the % weight loading of the AC-Ni catalyst, the % yield of Schiff base was also increased. The k app and Ti values were determined for the reduction of indole and a-terpineol in the presence of AC-Ni catalyst system. The experimental results were compared with the literature report.

show abstract

Facile Preparation of a Stable Fe₃O₄@LDH@NiB Magnetic Core‐Shell Nanocomposite for Hydrogenation

et al. 2017

View full text Add to dashboard Cite

A novel NiB deposited layered double hydroxide (LDH) coated ferroferric oxide (Fe 3 O 4 @LDH@NiB) magnetic core-shell nanocomposite was successfully fabricated by the combination of coprecipitation and impregnation-reduction. During the Fe 3 O 4 @LDH preparation, a facile template-free approach was employed to introduce the LDH shell, which was more efficient than the conventional method for the preparation of mesoporous materials that always needs to introduce and remove templates. The resulted Fe 3 O 4 @LDH has a relatively high surface area and abundant surface hydroxyl group, which can adsorb metal ions, making it favorable to disperse and stabilize the active Ni species, as demonstraed by TEM, XPS, FT-IR and BET characterizations. Therefore, it exhibited good activity in the selective hydrogenation of cinnamic acid to hydrocinnamic acid with the conversion and selectivity both approaching to 100%. Notably, the obtained Fe 3 O 4 @LDH@NiB can be easily separated by an external magnetic field and recycled eleven times without appreciable loss of its initial catalytic activity.

show abstract

Selective hydrogenation of unprotected indole to indoline over N-doped carbon supported palladium catalyst

Cited by 10 publications

References 51 publications

Palladium-Mediated Oxidative Annulation of δ-Indolyl-α,β-Unsaturated Compounds toward the Synthesis of Cyclopenta[b]indoles and Heterogeneous Hydrogenation To Access Fused Indolines

Palladium-Mediated Oxidative Annulation of δ-Indolyl-α,β-Unsaturated Compounds toward the Synthesis of Cyclopenta[b]indoles and Heterogeneous Hydrogenation To Access Fused Indolines

Synthesis, characterization and catalytic activity of nanosized Ni complexed aminoclay

Facile Preparation of a Stable Fe₃O₄@LDH@NiB Magnetic Core‐Shell Nanocomposite for Hydrogenation

Contact Info

Product

Resources

About

Selective hydrogenation of unprotected indole to indoline over N-doped carbon supported palladium catalyst

Cited by 10 publications

References 51 publications

Palladium-Mediated Oxidative Annulation of δ-Indolyl-α,β-Unsaturated Compounds toward the Synthesis of Cyclopenta[b]indoles and Heterogeneous Hydrogenation To Access Fused Indolines

Palladium-Mediated Oxidative Annulation of δ-Indolyl-α,β-Unsaturated Compounds toward the Synthesis of Cyclopenta[b]indoles and Heterogeneous Hydrogenation To Access Fused Indolines

Synthesis, characterization and catalytic activity of nanosized Ni complexed aminoclay

Facile Preparation of a Stable Fe3O4@LDH@NiB Magnetic Core‐Shell Nanocomposite for Hydrogenation

Contact Info

Product

Resources

About

Facile Preparation of a Stable Fe₃O₄@LDH@NiB Magnetic Core‐Shell Nanocomposite for Hydrogenation